NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.07
Volume:	229.284
LogP:	2.158
LogD:	2.417
LogS:	-3.861
# Rotatable Bonds:	0
TPSA:	70.16
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	2.699
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.968
MDCK Permeability:	1.4895813365001231e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	91.31044006347656%
Volume Distribution (VD):	0.545
Pgp-substrate:	6.639041900634766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.844
CYP2C19-inhibitor:	0.477
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.626
CYP3A4-inhibitor:	0.632
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	3.671
Half-life (T1/2):	0.543

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.337
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.581
Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.782
Skin Sensitization:	0.82
Carcinogencity:	0.195
Eye Corrosion:	0.018
Eye Irritation:	0.917
Respiratory Toxicity:	0.931

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC134848

Natural Product ID:	NPC134848
*Common Name:**	Bruceolline H
IUPAC Name:	6-hydroxy-3,3-dimethyl-4H-cyclopenta[b]indole-1,2-dione
Synonyms:	Bruceolline H
Standard InCHIKey:	JGPRUCFGUSXLES-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO3/c1-13(2)11-9(10(16)12(13)17)7-4-3-6(15)5-8(7)14-11/h3-5,14-15H,1-2H3
SMILES:	CC1(C)c2c(c3ccc(cc3[nH]2)O)C(=O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1922989
PubChem CID:	56833856
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[24199564]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[523096]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[523096]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[523096]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[523096]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[523096]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC134848 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	2976
0.2-0.3	13050
0.3-0.4	7098
0.4-0.5	14281
0.5-0.6	2617
0.6-0.7	1812
0.7-0.8	397
0.8-0.85	22
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9267	High Similarity	NPC12344
0.8571	High Similarity	NPC39679
0.852	High Similarity	NPC183777
0.849	Intermediate Similarity	NPC306376
0.8477	Intermediate Similarity	NPC86834
0.8477	Intermediate Similarity	NPC210828
0.8442	Intermediate Similarity	NPC23294
0.8392	Intermediate Similarity	NPC303951
0.835	Intermediate Similarity	NPC87413
0.8325	Intermediate Similarity	NPC67551
0.8276	Intermediate Similarity	NPC3207
0.8226	Intermediate Similarity	NPC72980
0.8222	Intermediate Similarity	NPC214106
0.8195	Intermediate Similarity	NPC247803
0.815	Intermediate Similarity	NPC4687
0.815	Intermediate Similarity	NPC249583
0.8116	Intermediate Similarity	NPC150239
0.8107	Intermediate Similarity	NPC264285
0.8098	Intermediate Similarity	NPC330009
0.8095	Intermediate Similarity	NPC212535
0.8073	Intermediate Similarity	NPC221873
0.8069	Intermediate Similarity	NPC325297
0.8051	Intermediate Similarity	NPC276517
0.8039	Intermediate Similarity	NPC219087
0.8029	Intermediate Similarity	NPC174760
0.8011	Intermediate Similarity	NPC474409
0.801	Intermediate Similarity	NPC94943
0.797	Intermediate Similarity	NPC270918
0.7962	Intermediate Similarity	NPC179287
0.7958	Intermediate Similarity	NPC190007
0.7951	Intermediate Similarity	NPC308137
0.7951	Intermediate Similarity	NPC310211
0.7943	Intermediate Similarity	NPC276657
0.794	Intermediate Similarity	NPC213308
0.7931	Intermediate Similarity	NPC171787
0.7927	Intermediate Similarity	NPC46580
0.7902	Intermediate Similarity	NPC9894
0.7882	Intermediate Similarity	NPC283117
0.7874	Intermediate Similarity	NPC116238
0.7867	Intermediate Similarity	NPC16352
0.7867	Intermediate Similarity	NPC220851
0.785	Intermediate Similarity	NPC194740
0.7837	Intermediate Similarity	NPC322064
0.7824	Intermediate Similarity	NPC132329
0.7816	Intermediate Similarity	NPC294375
0.781	Intermediate Similarity	NPC74360
0.7799	Intermediate Similarity	NPC293151
0.7799	Intermediate Similarity	NPC169402
0.7798	Intermediate Similarity	NPC473187
0.7794	Intermediate Similarity	NPC321428
0.7788	Intermediate Similarity	NPC118228
0.7762	Intermediate Similarity	NPC46561
0.7758	Intermediate Similarity	NPC178858
0.7746	Intermediate Similarity	NPC122436
0.7734	Intermediate Similarity	NPC476098
0.7725	Intermediate Similarity	NPC208084
0.77	Intermediate Similarity	NPC153042
0.77	Intermediate Similarity	NPC243834
0.77	Intermediate Similarity	NPC70956
0.7696	Intermediate Similarity	NPC96890
0.7692	Intermediate Similarity	NPC110182
0.7678	Intermediate Similarity	NPC303658
0.7667	Intermediate Similarity	NPC469928
0.7664	Intermediate Similarity	NPC51388
0.7659	Intermediate Similarity	NPC300156
0.7659	Intermediate Similarity	NPC45190
0.7656	Intermediate Similarity	NPC88363
0.7653	Intermediate Similarity	NPC198503
0.7653	Intermediate Similarity	NPC278434
0.763	Intermediate Similarity	NPC27041
0.7612	Intermediate Similarity	NPC141454
0.7611	Intermediate Similarity	NPC91868
0.7611	Intermediate Similarity	NPC63971
0.7602	Intermediate Similarity	NPC6786
0.7602	Intermediate Similarity	NPC160381
0.7594	Intermediate Similarity	NPC473041
0.7594	Intermediate Similarity	NPC184408
0.7592	Intermediate Similarity	NPC303225
0.759	Intermediate Similarity	NPC84478
0.7586	Intermediate Similarity	NPC45459
0.7586	Intermediate Similarity	NPC315491
0.7576	Intermediate Similarity	NPC154339
0.757	Intermediate Similarity	NPC60621
0.7561	Intermediate Similarity	NPC165599
0.755	Intermediate Similarity	NPC267343
0.7523	Intermediate Similarity	NPC235685
0.7523	Intermediate Similarity	NPC471762
0.7512	Intermediate Similarity	NPC291535
0.7512	Intermediate Similarity	NPC475085
0.7512	Intermediate Similarity	NPC135887
0.7512	Intermediate Similarity	NPC199277
0.7512	Intermediate Similarity	NPC475112
0.75	Intermediate Similarity	NPC74969
0.75	Intermediate Similarity	NPC207686
0.7489	Intermediate Similarity	NPC101350
0.7487	Intermediate Similarity	NPC83111
0.7478	Intermediate Similarity	NPC160898
0.7475	Intermediate Similarity	NPC206186
0.7465	Intermediate Similarity	NPC249428
0.7465	Intermediate Similarity	NPC305984
0.7462	Intermediate Similarity	NPC314002
0.746	Intermediate Similarity	NPC115232
0.7455	Intermediate Similarity	NPC260434
0.7455	Intermediate Similarity	NPC474701
0.7452	Intermediate Similarity	NPC88008
0.744	Intermediate Similarity	NPC132539
0.7429	Intermediate Similarity	NPC309845
0.7426	Intermediate Similarity	NPC326634
0.7424	Intermediate Similarity	NPC194040
0.7411	Intermediate Similarity	NPC204717
0.7406	Intermediate Similarity	NPC39500
0.7397	Intermediate Similarity	NPC478078
0.7395	Intermediate Similarity	NPC269270
0.7393	Intermediate Similarity	NPC187501
0.7387	Intermediate Similarity	NPC473105
0.7379	Intermediate Similarity	NPC471944
0.7374	Intermediate Similarity	NPC241025
0.7368	Intermediate Similarity	NPC193777
0.7368	Intermediate Similarity	NPC244741
0.7364	Intermediate Similarity	NPC66777
0.7364	Intermediate Similarity	NPC274640
0.7363	Intermediate Similarity	NPC138370
0.7361	Intermediate Similarity	NPC14686
0.736	Intermediate Similarity	NPC220765
0.7353	Intermediate Similarity	NPC156704
0.735	Intermediate Similarity	NPC128751
0.735	Intermediate Similarity	NPC246700
0.734	Intermediate Similarity	NPC131017
0.7337	Intermediate Similarity	NPC171171
0.7333	Intermediate Similarity	NPC111275
0.733	Intermediate Similarity	NPC252338
0.7327	Intermediate Similarity	NPC99666
0.7325	Intermediate Similarity	NPC78609
0.7321	Intermediate Similarity	NPC477549
0.7321	Intermediate Similarity	NPC175602
0.7317	Intermediate Similarity	NPC195457
0.7315	Intermediate Similarity	NPC288987
0.7313	Intermediate Similarity	NPC106833
0.7313	Intermediate Similarity	NPC469497
0.7308	Intermediate Similarity	NPC63109
0.7306	Intermediate Similarity	NPC97746
0.7304	Intermediate Similarity	NPC242209
0.7299	Intermediate Similarity	NPC61038
0.7296	Intermediate Similarity	NPC55772
0.7294	Intermediate Similarity	NPC144452
0.7282	Intermediate Similarity	NPC280714
0.7281	Intermediate Similarity	NPC323969
0.7281	Intermediate Similarity	NPC225279
0.7277	Intermediate Similarity	NPC97902
0.7268	Intermediate Similarity	NPC227582
0.7268	Intermediate Similarity	NPC74153
0.726	Intermediate Similarity	NPC229893
0.7256	Intermediate Similarity	NPC148183
0.7256	Intermediate Similarity	NPC152768
0.7255	Intermediate Similarity	NPC202812
0.7253	Intermediate Similarity	NPC244543
0.725	Intermediate Similarity	NPC99428
0.7245	Intermediate Similarity	NPC184964
0.7243	Intermediate Similarity	NPC89508
0.7238	Intermediate Similarity	NPC476106
0.7233	Intermediate Similarity	NPC472284
0.7233	Intermediate Similarity	NPC72211
0.7233	Intermediate Similarity	NPC131887
0.723	Intermediate Similarity	NPC146418
0.7227	Intermediate Similarity	NPC21638
0.722	Intermediate Similarity	NPC70259
0.7217	Intermediate Similarity	NPC469734
0.7212	Intermediate Similarity	NPC15801
0.7212	Intermediate Similarity	NPC476044
0.7206	Intermediate Similarity	NPC269886
0.7206	Intermediate Similarity	NPC247735
0.7206	Intermediate Similarity	NPC472295
0.7206	Intermediate Similarity	NPC81802
0.7206	Intermediate Similarity	NPC473821
0.7206	Intermediate Similarity	NPC106937
0.7206	Intermediate Similarity	NPC472210
0.7204	Intermediate Similarity	NPC53344
0.72	Intermediate Similarity	NPC182222
0.7198	Intermediate Similarity	NPC165964
0.7196	Intermediate Similarity	NPC48353
0.7196	Intermediate Similarity	NPC294620
0.7195	Intermediate Similarity	NPC214142
0.7195	Intermediate Similarity	NPC24370
0.7195	Intermediate Similarity	NPC319232
0.7189	Intermediate Similarity	NPC96321
0.7188	Intermediate Similarity	NPC279189
0.7188	Intermediate Similarity	NPC200553
0.7184	Intermediate Similarity	NPC90229
0.7181	Intermediate Similarity	NPC470784
0.7176	Intermediate Similarity	NPC85702
0.7171	Intermediate Similarity	NPC205934
0.7171	Intermediate Similarity	NPC43787
0.717	Intermediate Similarity	NPC475910
0.7169	Intermediate Similarity	NPC280799
0.7163	Intermediate Similarity	NPC207866
0.7163	Intermediate Similarity	NPC249040
0.7163	Intermediate Similarity	NPC31700
0.7163	Intermediate Similarity	NPC471080
0.7163	Intermediate Similarity	NPC469592
0.7162	Intermediate Similarity	NPC118559

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC134848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	664
0.2-0.3	872
0.3-0.4	1486
0.4-0.5	3165
0.5-0.6	2018
0.6-0.7	591
0.7-0.8	45
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7586	Intermediate Similarity	NPD484	Approved
0.7566	Intermediate Similarity	NPD2844	Phase 3
0.75	Intermediate Similarity	NPD2916	Discontinued
0.7371	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6376	Discontinued
0.7327	Intermediate Similarity	NPD5937	Approved
0.7318	Intermediate Similarity	NPD3259	Approved
0.7318	Intermediate Similarity	NPD4845	Discontinued
0.73	Intermediate Similarity	NPD4948	Discontinued
0.7297	Intermediate Similarity	NPD6962	Phase 2
0.7273	Intermediate Similarity	NPD5901	Discontinued
0.7264	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD8160	Phase 2
0.7232	Intermediate Similarity	NPD4373	Phase 2
0.7206	Intermediate Similarity	NPD802	Phase 2
0.72	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5632	Approved
0.7184	Intermediate Similarity	NPD7948	Phase 1
0.7175	Intermediate Similarity	NPD4952	Phase 3
0.7136	Intermediate Similarity	NPD4506	Discontinued
0.7136	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6242	Discontinued
0.7116	Intermediate Similarity	NPD8097	Phase 3
0.7116	Intermediate Similarity	NPD8096	Phase 3
0.7108	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5003	Discontinued
0.7098	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1326	Approved
0.7077	Intermediate Similarity	NPD1325	Approved
0.7056	Intermediate Similarity	NPD7941	Phase 3
0.7039	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3746	Discontinued
0.7028	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1592	Phase 3
0.701	Intermediate Similarity	NPD1534	Approved
0.7009	Intermediate Similarity	NPD2509	Approved
0.7009	Intermediate Similarity	NPD2510	Approved
0.7	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3258	Approved
0.6995	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5416	Discontinued
0.6979	Remote Similarity	NPD3986	Discontinued
0.6976	Remote Similarity	NPD2565	Phase 2
0.6976	Remote Similarity	NPD4499	Approved
0.6976	Remote Similarity	NPD2564	Approved
0.697	Remote Similarity	NPD482	Approved
0.697	Remote Similarity	NPD6790	Phase 1
0.6959	Remote Similarity	NPD1631	Approved
0.6957	Remote Similarity	NPD1038	Approved
0.6952	Remote Similarity	NPD8396	Approved
0.6952	Remote Similarity	NPD8395	Approved
0.6952	Remote Similarity	NPD1768	Approved
0.695	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6987	Phase 1
0.693	Remote Similarity	NPD5658	Approved
0.6927	Remote Similarity	NPD3243	Approved
0.6916	Remote Similarity	NPD3003	Approved
0.6912	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6995	Phase 1
0.6904	Remote Similarity	NPD1573	Approved
0.6904	Remote Similarity	NPD1575	Approved
0.6901	Remote Similarity	NPD6176	Phase 1
0.6901	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3257	Approved
0.689	Remote Similarity	NPD5512	Phase 3
0.6889	Remote Similarity	NPD7603	Discontinued
0.6887	Remote Similarity	NPD4511	Phase 1
0.6884	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3814	Phase 1
0.6856	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5293	Phase 2
0.6814	Remote Similarity	NPD2096	Phase 2
0.6814	Remote Similarity	NPD2091	Phase 2
0.6812	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1630	Approved
0.6802	Remote Similarity	NPD7878	Phase 2
0.6798	Remote Similarity	NPD3178	Discontinued
0.6791	Remote Similarity	NPD3947	Discontinued
0.6791	Remote Similarity	NPD8098	Approved
0.6787	Remote Similarity	NPD3389	Approved
0.6787	Remote Similarity	NPD3393	Approved
0.6787	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD3394	Approved
0.6786	Remote Similarity	NPD5138	Approved
0.6786	Remote Similarity	NPD5140	Approved
0.6784	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4561	Discontinued
0.6773	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6770	Approved
0.677	Remote Similarity	NPD3925	Approved
0.6765	Remote Similarity	NPD5482	Discontinued
0.6765	Remote Similarity	NPD2095	Phase 2
0.6765	Remote Similarity	NPD2092	Phase 2
0.6765	Remote Similarity	NPD2094	Phase 2
0.6759	Remote Similarity	NPD3507	Phase 2
0.6756	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.675	Remote Similarity	NPD750	Phase 2
0.6745	Remote Similarity	NPD7946	Pre-registration
0.6739	Remote Similarity	NPD4885	Approved
0.6735	Remote Similarity	NPD1684	Approved
0.6735	Remote Similarity	NPD1685	Approved
0.6728	Remote Similarity	NPD1392	Approved
0.6726	Remote Similarity	NPD4429	Discontinued
0.6724	Remote Similarity	NPD7853	Phase 2
0.6715	Remote Similarity	NPD2383	Phase 1
0.6714	Remote Similarity	NPD6999	Discontinued
0.6714	Remote Similarity	NPD2176	Approved
0.6714	Remote Similarity	NPD2177	Approved
0.6714	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2175	Phase 3
0.6714	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5426	Phase 3
0.6713	Remote Similarity	NPD8283	Approved
0.6713	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD8282	Approved
0.6713	Remote Similarity	NPD56	Approved
0.6711	Remote Similarity	NPD4328	Approved
0.6711	Remote Similarity	NPD7994	Phase 2
0.67	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1587	Approved
0.6696	Remote Similarity	NPD1867	Approved
0.6696	Remote Similarity	NPD1505	Phase 2
0.6696	Remote Similarity	NPD4312	Approved
0.6682	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7001	Phase 3
0.6682	Remote Similarity	NPD4600	Approved
0.6682	Remote Similarity	NPD4601	Approved
0.668	Remote Similarity	NPD7181	Phase 3
0.6667	Remote Similarity	NPD8091	Phase 3
0.6667	Remote Similarity	NPD5903	Approved
0.6667	Remote Similarity	NPD5902	Approved
0.6667	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5445	Approved
0.6652	Remote Similarity	NPD3006	Discontinued
0.6652	Remote Similarity	NPD5479	Discontinued
0.6638	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5612	Discontinued
0.6637	Remote Similarity	NPD6733	Discontinued
0.6636	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8364	Approved
0.6627	Remote Similarity	NPD8363	Approved
0.6624	Remote Similarity	NPD4368	Phase 2
0.6624	Remote Similarity	NPD5805	Approved
0.6619	Remote Similarity	NPD2336	Approved
0.6612	Remote Similarity	NPD6531	Approved
0.6612	Remote Similarity	NPD6530	Approved
0.661	Remote Similarity	NPD7417	Discontinued
0.6606	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7470	Discontinued
0.6605	Remote Similarity	NPD4500	Approved
0.6605	Remote Similarity	NPD4501	Approved
0.6604	Remote Similarity	NPD4418	Discontinued
0.6602	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3962	Phase 2
0.6597	Remote Similarity	NPD3959	Phase 2
0.6595	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2920	Discontinued
0.6585	Remote Similarity	NPD1643	Phase 3
0.6582	Remote Similarity	NPD6716	Phase 1
0.6582	Remote Similarity	NPD6517	Phase 3
0.658	Remote Similarity	NPD5022	Discontinued
0.6577	Remote Similarity	NPD2794	Discontinued
0.6574	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7803	Approved
0.6573	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6159	Phase 2
0.6569	Remote Similarity	NPD7865	Approved
0.6566	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1586	Approved
0.6552	Remote Similarity	NPD5065	Approved
0.6548	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8423	Phase 2
0.6545	Remote Similarity	NPD8399	Phase 1
0.6542	Remote Similarity	NPD8358	Approved
0.654	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8466	Approved
0.6535	Remote Similarity	NPD8428	Approved
0.6535	Remote Similarity	NPD8465	Approved
0.6535	Remote Similarity	NPD8427	Approved
0.6535	Remote Similarity	NPD8467	Approved
0.6535	Remote Similarity	NPD8429	Approved
0.6533	Remote Similarity	NPD5164	Discontinued
0.6532	Remote Similarity	NPD5939	Approved
0.6532	Remote Similarity	NPD5936	Approved
0.6528	Remote Similarity	NPD5879	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2792	Approved
0.6522	Remote Similarity	NPD3319	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data